N-(2,2-Dimethyl-1,3-dioxan-5-yl)-6-methoxy-3-nitropyridin-2-amine → N2-(2,2-Dimethyl-1,3-dioxan-5-yl)-6-methoxypyridine-2,3-diamine

HRID 420678Notes

Reaction equation

HRID 420678 reaction equation
[CH3:1][C:2]1([CH3:20])[O:7][CH2:6][CH:5]([NH:8][C:9]2[C:14]([N+:15]([O-])=O)=[CH:13][CH:12]=[C:11]([O:18][CH3:19])[N:10]=2)[CH2:4][O:3]1.[H][H]>O1CCOCC1.[Pd]>[CH3:1][C:2]1([CH3:20])[O:7][CH2:6][CH:5]([NH:8][C:9]2[C:14]([NH2:15])=[CH:13][CH:12]=[C:11]([O:18][CH3:19])[N:10]=2)[CH2:4][O:3]1

Participants

5

Reactant 2

HCID 58001746N-(2,2-Dimethyl-1,3-dioxan-5-yl)-6-methoxy-3-nitropyridin-2-amineHCID 178418361HCID 178418361, compound

Product 1

HCID 58001800N2-(2,2-Dimethyl-1,3-dioxan-5-yl)-6-methoxypyridine-2,3-diamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

N-(2,2-Dimethyl-1,3-dioxan-5-yl)-6-(methyloxy)-3-nitro-2-pyridinamine (35.00 g, 123.6 mmol) was divided into 2 aliquots, each of which was taken up in 1,4-dioxane (500 ml) and hydrogenated over 10% Pd on carbon (paste, 1:1 w:w with water, 4.00 g) under 1 atmosphere hydrogen pressure, at room temperature for 18 h. The mixtures were filtered with suction though Celite, using argon blanket and taking care to minimise contact of the product with air. The solids were washed with 1,4-dioxane and the combined filtrate plus washings were evaporated under reduced pressure to give the title compound as a deep purple oil. This was used immediately in the next step.

Workup

  1. filtrationThe mixtures were filtered with suction though Celite
  2. washThe solids were washed with 1,4-dioxane
  3. customthe combined filtrate plus washings were evaporated under reduced pressure

Sources & evidence

ORD record
ord-ed41801681504b6dbe9967853c6c911d
Source dataset
uspto-grants-2012_01
Patent number
US08097628B2

Reaction notes

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